Leading Teams and Delighting Customers

Tag: Ryan Holiday

Build Your Own Red Team

At some point or another, I’d imagine virtually all of us have answered some form of the “money is no object” question. Essentially this: If you didn’t have to worry about money at all, what would you do?

My standard reply is to open some form of bookstore and coffee shop.

There would be no WiFi, and we’d stack the whole place with good old-fashioned physical books. If we want to get really specific, I’d name it “Penny University,” a callback to English coffeehouses in the 17th and 18th century. Oh, and we’d have monthly discussions where we call in experts to debate both sides of a “hot topic” (education, politics, poverty, future of work, etc).

I’ve thought about this a lot!

As much as I love this idea though, I’m probably not going to open a bookstore. The whole thing just feels so risky, especially as we talk about a worldwide pandemic (setting aside the ebook vs. physical book discussion).

Imagine my shock and delight when I read about Ryan Holiday’s new bookstore outside of Austin, Texas—The Painted Porch. He wrote a piece for the Texas Monthly aptly titled “Opening a Small-Town Bookstore During the Pandemic Was the Craziest Thing We Ever Did.

Sounds accurate.

The whole experience was fascinating, but one piece stuck out, what I would equate to a version of red teaming:

Whenever I’m considering an idea I’m excited about, I like to ask friends to talk me out of it.

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The Obstacle is the Way

Author: Ryan Holiday
Title: The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph
Published: May 1, 2014

I’ve been a huge fan of Holiday’s work since I first stumbled across his blog. I thoroughly enjoyed his first book, Trust Me, I’m Lying: Confessions of a Media Manipulator, and his short primer on Growth Hacker Marketing. Having read quite a bit of his work, I always appreciate his unusual aspect on various subjects. When Holiday announced that he was putting out a new book concerning overcoming obstacles and guidance from his favorite Stoic authors, I was intrigued.

The book is largely based on the philosophy of Stoicism, which is a practice of deep reflection, emotion regulation, and focused action used to appreciate, benefit, and dominate the world around you. Holiday draws on examples from famous historic figures like Ulysses S. Grant and George Washington. He references the work of Marcus Aurelius and Epictetus. In each case, Holiday is helping readers to understand how even the most horrid of situations can be flipped to become an advantage. Take, for example, the story of Thomas Edison:

At age sixty-seven , Thomas Edison returned home early one evening from another day at the laboratory. Shortly after dinner, a man came rushing into his house with urgent news: A fire had broken out at Edison’s research and production campus a few miles away.

Fire engines from eight nearby towns rushed to the scene, but they could not contain the blaze. Fueled by the strange chemicals in the various buildings, green and yellow flames shot up six and seven stories, threatening to destroy the entire empire Edison had spent his life building.

Edison calmly but quickly made his way to the fire, through the now hundreds of onlookers and devastated employees, looking for his son. “Go get your mother and all her friends,” he told his son with childlike excitement. “They’ll never see a fire like this again.” (Kindle Locations 1777-1783)

Despite that setback that year, Edison went on to generate a revenue of $10 million from his lab, quite the comeback from having everything you’ve ever worked on burned to the ground.

Holiday outlines how to overcome obstacles we will all face in our own lives in three parts:

  1. Perception – Flipping how we see and understand what is happening around us
  2. Action – How to create directed action to achieve what we’re looking for
  3. Will – How we keep moving forward even when it seems like we have no control over the situation and our backs are against the wall

Per the usual for Holiday’s writing, the work is absolutely filled with research and references. I always appreciate how well he backs up his thoughts with quotes and anecdotes from the past. Don’t go into this book expecting a step-by-step solution to getting what you want. Instead, Holiday presents a framework designed to help you change how you approach situations and how to make the best of the worst circumstances.

At a time where it’s easy to feel overwhelmed and helpless against powerful opposition, this book is a roadmap for achieving. I’d highly recommend it to anyone looking for a new perspective on how to shape your thoughts and actions to be more successful.

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